Water-soluble condensation product and process of making same



ltd

Patented Oct. 22, .1929

UNITED STATES PATENT OFFICE KARL DACHLAUER AND CHRISTOPH THOMSEN', 0F HOCHS'I-ON-THE-MAIN, GERMANY,

ASSIG'NORS TO I. G. FABBENINIDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFURT- ON-THE-MAIN, GERMANY, A CORPORATION OF GERMANY WATER-SOLUBLE CONDENSATIOLN PRODUCT AND PROCESS OF'M AKING SAME No Drawing. Application filed. March 5, 1926, Serial No. 92,583, and in Germany March 0, 1025.

The object of our present invention is the preparation of water-soluble condensation products from halogenated organic carbonylcontaining compounds and aromatic hydroxy compounds, I

We have found that the said condensation products from halogenated organic compounds containing carbonyl and aromatic hydroxy compounds, which are insoluble in water, can be transformed into water-soluble products which possess excellent froth-forming and emulsifying properties and are capable of transforming animal hides into leather of excellent quality. Moreover, by means of the said. products it is possible to produce on the animal fibre eficient resists against dyestuffs.

The mostsuitable compounds containing a carbonyl for carrying out our invention are simple or mixed halogenated ketones or aldehydes and they may be used either alone or in mixture. The derivatives of the said compounds, of course, also fall within the scope of our invention.

llnstead of the halogenated ketones or alde 01120101101.opens-300E501!=H2o+Ho1+ozmcn nooumonaon The transformation of these condensation products into water-soluble products may be carried out by any of the known methods, for instance by sulfonation. As sulfonating agent may be employed among others, contives as they arise for instance during their preparation. 7 t

The following examples serve toillustrate' our invention:

1. Into 12.3 kg. of phenol are slowly introduced at 100U, while stirring, t kg. of chloracetoue and 8 kg. of concentrated hydrochloric acid. After the condensation is complete, the hydrochloric acid is eliminated by washing and the product is then sulfonated at about 95 C. with 10 kg. of sulfuric acid of 96% strength, while stirring.

The phenol may be replaced by tricresol or crude coal-tar phenol. Any uncondensed portions may be separated by steam distillation prior to the sulfonation.

2. Into 11.3 kg. of phenol are slowly introduced at 100 (3., while stirring, 3.1 kg.

of chloroacetaldehyde and 6 kg. of cone.

hydrochloric acid. After the condensation is complete and the hydrochloric acid has been eliminated by washing, the product is sultonat ed with 8 kg. of concentrated sulfuric acid at about 95 C.

The phenol may also in this case be replaced by tricresol or crude coal-tar phenol and the chloracetaldehyde for instance by dichlorether.

'3. Into 10 kg. of phenol are run at 100 C. 5.1 kg. of asymmetrical dichlorether and this mixture is heated, while stirring, until the evolution of hydrochloric acid and ethyl chloride has ceased. -The condensation CsH4.OH

otmon product is sulfonated while hot with 7 :8 kg. of concentrated sulfuric acid.

4. Into 1 4.1 kg. of phenol are introduced at 100 (1, while stirring, 4.6 kg. of chloracetone and 8.9 kg. of conci. hydrochloric centratedsulfuric acid or chlorosulfonic acid. b acid. "When the condensation is complete and Some of the products are colored and can be the hydrochloric acid has been eliminated by clarified or decolorized by a suitable treatwashing, the condensation product is heated ment, for instance by means of a reducing for some hours on the water-bath together agent. with 14.9 kg. of crystallized sodium sulfite, lnstead of the halogen derivatives alone, 29.7 kg. of water and 4.42 kg. of formaldehyde there may also be used mixtures of aldehydes, of 40% strength until the whole has entirely ketones or ethers with their halogen derivadissolved. f

5. Into 33.8 kg. of phenol are slowly run at" 100 0., while stirring, 10.7 kg. of

chlorethylinet-hylketone together with about 30 kg. of concentrated hydroehloric acid and this mixture is stirred at the sametempe-rature until the reaction is complete. -After the condensation product has been separated from the aqueous hydrochloric acid and washed with water, it is treated with 20 kg. of concentrated sulfuric acid at about 95 (1., while stirring, until it becomes soluble in water.

I The new products of the present invention may be represented by the following general formula:

wherein X represents hydrogen or an alkyl radical, the hydrogen atoms of which may be furthersubstituted, and Y represents one of the groups SO H or aIkyLSO H.

We claim:

1. As new products, the compounds of the following formula:

wherein X represents hydrogen or an alkyl radical, the hydrogen atoms of which may be further substituted, and Y represents one of the groupsSO' H oralkyLSO H.

2. As new products, the compounds of the following formula:

wherein X represents hydrogen or an alkyl radical, the hydrogen atoms of which may be further substituted, and Y represents one of the groups SO H or aIkyLSO H.

3. As new products, the compounds ofthe following formula where in X represents hydrogen or an alkyl radical, the hydrogen atoms of which may be further substituted, and Y represents one of the groups- SO H or alkyLSO H.

4. As a new product, a compound of the following formula In testimony whereof, we afiix our signatures.

DR. KARL DACHLAUER; DB. CHRISTOPH THOMSEN. 

